diff --git a/hermes_cli/update_cmd.py b/hermes_cli/update_cmd.py
index a1f5873f007ce..092504d75b399 100644
--- a/hermes_cli/update_cmd.py
+++ b/hermes_cli/update_cmd.py
@@ -188,6 +188,11 @@ def _validate_critical_modules_import(root) -> tuple[bool, str | None, str | Non
     updater would pollute ``sys.modules`` and execute import-time side effects
     against the half-updated tree. Costs ~0.4s.
 
+    Uses the project venv's interpreter when there is one (matching
+    ``_venv_core_imports_healthy``): ``hermes update`` can be driven by a
+    different Python than the install's own, and probing the wrong
+    interpreter would test a tree the user never runs.
+
     Returns ``(ok, failing_module, error_message)``.
     """
     probe = (
@@ -203,8 +208,17 @@ def _validate_critical_modules_import(root) -> tuple[bool, str | None, str | Non
         "raise SystemExit(0)\n" % (_UPDATE_CRITICAL_MODULES,)
     )
     try:
+        interpreter = sys.executable
+        try:
+            bin_dir = "Scripts" if _m()._is_windows() else "bin"
+            python_name = "python.exe" if _m()._is_windows() else "python"
+            venv_python = Path(root) / "venv" / bin_dir / python_name
+            if venv_python.exists():
+                interpreter = str(venv_python)
+        except Exception:
+            pass  # fall back to the running interpreter
         result = subprocess.run(
-            [sys.executable, "-c", probe],
+            [interpreter, "-c", probe],
             cwd=str(root),
             capture_output=True,
             text=True,
diff --git a/tests/hermes_cli/test_update_import_guard.py b/tests/hermes_cli/test_update_import_guard.py
index 1a0327095701c..61827fa4694f8 100644
--- a/tests/hermes_cli/test_update_import_guard.py
+++ b/tests/hermes_cli/test_update_import_guard.py
@@ -115,3 +115,35 @@ def test_hint_stays_silent_for_unrelated_failures(exc):
     if isinstance(exc, ImportError) and not isinstance(exc, ModuleNotFoundError):
         exc.name = "requests"
     assert partial_update_hint(exc) == []
+
+
+def test_import_guard_prefers_the_project_venv_interpreter(monkeypatch, tmp_path):
+    """``hermes update`` can run under a different Python than the install's.
+
+    Probing ``sys.executable`` would then validate a tree the user never
+    actually runs -- the same reasoning behind ``_venv_core_imports_healthy``.
+    On Windows (the platform this guard exists for) the driving interpreter
+    and the venv interpreter routinely differ.
+    """
+    bin_dir = "Scripts" if update_cmd._m()._is_windows() else "bin"
+    name = "python.exe" if update_cmd._m()._is_windows() else "python"
+    venv_python = tmp_path / "venv" / bin_dir / name
+    venv_python.parent.mkdir(parents=True)
+    venv_python.write_text("")
+
+    seen: dict = {}
+
+    def fake_run(cmd, **kwargs):
+        seen["interpreter"] = cmd[0]
+
+        class R:
+            returncode = 0
+            stdout = ""
+            stderr = ""
+
+        return R()
+
+    monkeypatch.setattr(update_cmd.subprocess, "run", fake_run)
+    update_cmd._validate_critical_modules_import(tmp_path)
+
+    assert seen["interpreter"] == str(venv_python)